Synthesis of 4-aryl-azetidinones via intramolecular alkylation of nucleophilic arenes using acyliminium cations

The acyliminium cations derived from 4-vinyloxy- or 4-acyloxy-azetidin-2-ones in the presence of Lewis acids can alkylate nucleophilic arenes bound to the β-lactam nitrogen atom through methyloxy, or methylthio tethers. The reactions smoothly proceed to afford the corresponding 3-oxa- or 3-thia-4,5-...

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Bibliographic Details
Published in:Tetrahedron 2010-11, Vol.66 (46), p.8974-8981
Main Authors: Zambroń, Bartosz, Masnyk, Marek, Furman, Bartłomiej, Kalicki, Przemysław, Chmielewski, Marek
Format: Article
Language:English
Subjects:
Acyliminium cations
Chemistry
Electrophilic aromatic substitution
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
β-Lactams
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Summary:The acyliminium cations derived from 4-vinyloxy- or 4-acyloxy-azetidin-2-ones in the presence of Lewis acids can alkylate nucleophilic arenes bound to the β-lactam nitrogen atom through methyloxy, or methylthio tethers. The reactions smoothly proceed to afford the corresponding 3-oxa- or 3-thia-4,5-benzocephams in a good yield. The sulfur atom can be easily removed by Raney nickel reduction to provide the title compounds. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.09.024